Deal found on October 29, 2026
Chicago to San Juan
$207$31234% off
Round trip
San Juan nonstop from Chicago is just $207 round trip, well under the usual $360 to $476. With 15 different date combinations open from November 2026 through April 2027, there's plenty of flexibility to catch some Caribbean sun at this fire price.
Travel dates
February into March
e.g. Feb 23 – Mar 4 · 9 nights
Date options
15 at this price
Lowest we've seen
$128
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